Make the cupcakes:
Preheat the oven to 350ºF. Line a cupcake pan with liners.
In the bowl of a stand mixer fitted with the paddle attachment, beat together the oil, buttermilk, eggs, white vinegar, vanilla extract and enough red food coloring until the mixture is well combined and reaches your desired color.
In a separate medium bowl, sift together the flour, sugar, baking soda, salt and cocoa powder.
Add the dry ingredients to the wet ingredients, 1/2 a cup at a time, mixing between each addition to avoid any lumps in the batter.
Fill each cupcake liner about 3/4 full with batter and bake for 18 to 20 minutes until a toothpick inserted comes out clean. Transfer the cupcakes to a cooling rack to cool completely while you make the frosting.
Make the frosting:
In the bowl of a stand mixer fitted with the paddle attachment, beat the cream cheese until smooth. Sift the powdered sugar into the bowl, beating to combine, then add the vanilla extract.
Remove the paddle attachment and attach the whisk attachment. Scrape down any cream cheese from the sides of the bowl, and then with the whisk beating at medium-high speed, stream in the cold heavy cream until the frosting is thick enough to pipe.
Transfer the frosting to a piping bag fitted with your desired pastry tip. Pipe the frosting onto the cooled cupcakes and serve immediately.
To get the deep, dark red color in the photos, I use a gel-based food coloring. Regular water-based food colorings are less concentrated and thus require more to achieve the same rich color. If you are using the water-based food coloring in this recipe, you'll need about 3 tablespoons to achieve a good color. If you're using the gel-based food coloring, start with 4 to 5 drops and add more as needed.
This frosting recipe makes enough to pipe tall, thick swirls onto the cupcakes. If you'd rather slather the cupcakes using less frosting, divide the frosting recipe in half.
You must use a brand of heavy cream that whips easily into stiff peaks. If you're uncertain your heavy cream whips easily, whip the heavy cream separate from the cream cheese (until it reaches stiff peaks) and then fold it into the cream cheese.